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Cheap flights from Illinois to Anguilla from $301

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Anguilla departing on 1/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Illinois to Anguilla

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:59 pm - 1:23 pm
ORD
-
AXA
17h 24m1 stop
American Airlines Logo
4:18 pm - 10:55 am
AXA
-
ORD
19h 37m1 stop
$542American Airlines
Mon, Mar 23 - Tue, Mar 31
American Airlines Logo
7:00 am - 4:44 pm
ORD
-
AXA
7h 44m1 stop
American Airlines Logo
5:24 pm - 12:33 am
AXA
-
ORD
9h 09m1 stop
$573American Airlines
Sun, Feb 22 - Wed, Feb 25
American Airlines Logo
7:00 am - 3:38 pm
ORD
-
AXA
7h 38m1 stop
American Airlines Logo
4:18 pm - 7:21 am
AXA
-
ORD
16h 03m2 stops
$574American Airlines
Mon, Mar 23 - Tue, Mar 31
American Airlines Logo
8:56 pm - 2:19 pm
ORD
-
AXA
15h 23m2 stops
American Airlines Logo
5:24 pm - 7:20 am
AXA
-
ORD
15h 56m2 stops
$578American Airlines
Sun, Feb 22 - Wed, Feb 25
American Airlines Logo
7:13 pm - 2:19 pm
ORD
-
AXA
17h 06m1 stop
American Airlines Logo
5:24 pm - 9:02 am
AXA
-
ORD
17h 38m1 stop
$598American Airlines
Thu, Feb 26 - Thu, Mar 5
American Airlines Logo
9:02 pm - 2:19 pm
ORD
-
AXA
15h 17m2 stops
American Airlines Logo
5:24 pm - 7:20 am
AXA
-
ORD
15h 56m2 stops
$603American Airlines
Thu, Feb 26 - Thu, Mar 5
American Airlines Logo
7:17 pm - 1:10 pm
ORD
-
AXA
16h 53m1 stop
American Airlines Logo
4:05 pm - 7:10 am
AXA
-
ORD
16h 05m2 stops
$611American Airlines
Sat, Apr 25 - Sat, May 2
American Airlines Logo
5:00 am - 3:38 pm
ORD
-
AXA
9h 38m2 stops
American Airlines Logo
4:18 pm - 7:21 am
AXA
-
ORD
16h 03m2 stops
$614American Airlines
Mon, Mar 23 - Tue, Mar 31
American Airlines Logo
7:00 am - 4:26 pm
ORD
-
AXA
7h 26m1 stop
American Airlines Logo
5:24 pm - 8:48 am
AXA
-
ORD
17h 24m1 stop
$628American Airlines
Mon, Feb 9 - Mon, Feb 16
American Airlines Logo
8:49 pm - 2:23 pm
ORD
-
AXA
15h 34m2 stops
American Airlines Logo
5:24 pm - 8:48 am
AXA
-
ORD
17h 24m1 stop
$633American Airlines
Mon, Feb 9 - Mon, Feb 16

American Airlines flights from Illinois to Anguilla

Our best American Airlines deals on Illinois to Anguilla flight tickets
American Airlines
Mar 23
ORD6:59 pmChicago O'Hare Intl
17h 24m
1 stop
AXA1:23 pmThe Valley Wallblake Intl
Mar 31
AXA4:18 pmThe Valley Wallblake Intl
19h 37m
1 stop
ORD10:55 amChicago O'Hare Intl
$542
Find similar
American Airlines
Feb 22
ORD7:00 amChicago O'Hare Intl
7h 44m
1 stop
AXA4:44 pmThe Valley Wallblake Intl
Feb 25
AXA5:24 pmThe Valley Wallblake Intl
9h 09m
1 stop
ORD12:33 amChicago O'Hare Intl
$573
Find similar
American Airlines
Mar 23
ORD7:00 amChicago O'Hare Intl
7h 38m
1 stop
AXA3:38 pmThe Valley Wallblake Intl
Mar 31
AXA4:18 pmThe Valley Wallblake Intl
16h 03m
2 stops
ORD7:21 amChicago O'Hare Intl
$574
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Anguilla that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 27, 2025.
Use the filters below to find and compare flights from Illinois to Anguilla that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 3/23

6:59 pm-1:23 pm

1 stop17h 24m

The Valley Wallblake Intl

Tue 3/31

4:18 pm-10:55 am

1 stop19h 37m

$542

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 2/22

7:00 am-4:44 pm

1 stop7h 44m

The Valley Wallblake Intl

Wed 2/25

5:24 pm-12:33 am

1 stop9h 09m

$573

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 3/23

7:00 am-3:38 pm

1 stop7h 38m

The Valley Wallblake Intl

Tue 3/31

4:18 pm-7:21 am

2 stops16h 03m

$574

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 2/22

8:56 pm-2:19 pm

2 stops15h 23m

The Valley Wallblake Intl

Wed 2/25

5:24 pm-7:20 am

2 stops15h 56m

$578

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 2/26

7:13 pm-2:19 pm

1 stop17h 06m

The Valley Wallblake Intl

Thu 3/5

5:24 pm-9:02 am

1 stop17h 38m

$598

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 2/26

9:02 pm-2:19 pm

2 stops15h 17m

The Valley Wallblake Intl

Thu 3/5

5:24 pm-7:20 am

2 stops15h 56m

$603

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 4/25

7:17 pm-1:10 pm

1 stop16h 53m

The Valley Wallblake Intl

Sat 5/2

4:05 pm-7:10 am

2 stops16h 05m

$611

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 3/23

5:00 am-3:38 pm

2 stops9h 38m

The Valley Wallblake Intl

Tue 3/31

4:18 pm-7:21 am

2 stops16h 03m

$614

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 2/9

7:00 am-4:26 pm

1 stop7h 26m

The Valley Wallblake Intl

Mon 2/16

5:24 pm-8:48 am

1 stop17h 24m

$628

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 2/9

8:49 pm-2:23 pm

2 stops15h 34m

The Valley Wallblake Intl

Mon 2/16

5:24 pm-8:48 am

1 stop17h 24m

$633

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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See travel insights to Anguilla from

How to get the cheapest flight ticket from Illinois to Anguilla

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Anguilla?

The cheapest day to depart from Illinois to Anguilla is on a Friday when prices can be found for as low as $650. The most expensive day to fly to Anguilla is Saturday, with ticket prices averaging around $990.

What is the cheapest time of day to depart on your flight to Anguilla?

Flying to Anguilla from Illinois in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $607 when looking at flights departing in the afternoon. Flights in the morning are often more expensive with an average ticket price of $759.

Cheap Illinois to Anguilla flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Anguilla

Fastest flight time

9h 55m

Direct flights

None
The fastest flight from Illinois to Anguilla takes 9h 55m
There are no direct flights from Illinois to Anguilla. There are no popular flight routes from Illinois to Anguilla.
Search flight deals

  • When did momondo last update prices for flights from Illinois to Anguilla?

    Prices for flights from Illinois to Anguilla refresh daily.

  • How many operators does momondo search for flights from Illinois to Anguilla?

  • How old do you have to be to fly from Illinois to Anguilla?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Anguilla.

  • What documentation or ID do you need to fly to Anguilla?

    The required travel and health documents for your Anguilla trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Anguilla. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Illinois to Anguilla

Compare and see reviews for airlines that fly from Illinois to Anguilla with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $597Free CancellationRating
7.2
11,067 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Anguilla?

It is quick and easy to find Illinois to Anguilla flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Anguilla that suits you.

Can I find flights from Illinois to Anguilla with flexible booking policies on momondo?

All flight searches from Illinois to Anguilla on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Illinois to Anguilla?

momondo provides multiple filters to help you find the best flight to Anguilla from Illinois. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Illinois to Anguilla right now. Can momondo alert me if prices change?

Price alerts on flights to Anguilla from Illinois are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Popular cities in Anguilla

Popular flights according to clicks in the last 7 days on momondo
Flights to The Valleyfrom $464